156629-27-5Relevant academic research and scientific papers
Synthesis of a chiral steroid ring D precursor starting from carvone
Pogrebnoi, Serghei,Sarabèr, Florence C. E.,Jansen, Ben J. M.,De Groot, Aede
, p. 1743 - 1748 (2006)
A chiral five-membered, silyl enol ether containing, steroid ring D precursor has been synthesized from carvone. This silyl enol ether has been applied in the synthesis of a chiral C17 functionalized steroid skeleton using the addition of a carbocation, g
Study towards diversity oriented synthesis of optically active substituted cyclopentane fused carbocyclic and oxacyclic medium-sized rings: Competition between Grubbs-II catalyzed ring closing olefin metathesis and ring closing carbonyl-olefin metathesis
Chakraborty,Roy
, p. 1831 - 1840 (2016)
A study towards diversity-oriented synthesis of optically active cyclopentane fused bicyclic frameworks has been accomplished. The common intermediate was prepared from commercially available starting material (S)-carvone. The observations on competition
The search for new odorants: Synthesis of animalic fragrant and musky/ambery compounds
Plessis, Caroline
, p. 1517 - 1539 (2015/03/03)
An overview of the recent research which allowed us to discover novel animalic odorants is presented. The new derivatives were prepared from readily available starting materials via easy reaction steps in good yields. They possess very different structures, such as bicyclic pentanols, glycolates, or tricyclic ketones, and all show interesting notes in the animalic fragrant family: from costus, leathery to ambery and musky scents, making them all attractive for different purposes.
Concise total synthesis of (-)-8-epigrosheimin
Yang, Haishen,Gao, Yuzhe,Qiao, Xiaoxiao,Xie, Longguan,Xu, Xiaohua
, p. 3670 - 3673 (2011/09/15)
A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.
Diastereoselective total synthesis of 8-epigrosheimin
Yang, Haishen,Qiao, Xiaoxiao,Li, Fangyi,Ma, Hui,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 1110 - 1112 (2009/05/27)
The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated γ-butyrolactone ring. Our approach featured that the γ-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative γ-lactonization; and (3) an intramolecular aldehyde-ene cyclization.
Total synthesis of five thapsigargins: Guaianolide natural products exhibiting sub-nanomolar SERCA inhibition
Andrews, Stephen P.,Ball, Matthew,Wierschem, Frank,Cleator, Ed,Oliver, Steven,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Huenger, Udo,Smith, Martin D.,Ley, Steven V.
, p. 5688 - 5712 (2008/02/13)
Herein we describe the total synthesis of five guaianolide natural products: thapsigargin. thapsivillosin C, thapsivillosin F, trilobolide and nortrilobolide. Prodrug derivatives of thapsigargin have shown selective in vivo cytotoxicity against prostate tumours and the need for further investigation of this phenomenon highlights the importance of these total syntheses. The first absolute stereochemical assignment of thapsivillosin C is also delineated.
A Route to the Thapsigargins from (S)-Carvone Providing a Substrate-Controlled Total Synthesis of Trilobolide, Nortrilobolide, and Thapsivillosin F
Oliver, Steven F.,Hoegenauer, Klemens,Simic, Oliver,Antonello, Alessandra,Smith, Martin D.,Ley, Steven V.
, p. 5996 - 6000 (2007/10/03)
An entirely substrate-controlled total synthesis of three members of the thapsigargin family (e.g. trilobolide) is achieved starting from (S)-carvone. The synthesis is linear in nature but is achieved in high yield (> 90% per step). The route permits late
Stereoselective Favorskii Rearrangement of Carvone Chlorohydrin; Expedient Synthesis of (+)-Dihydronepetalactone and (+)-Iridomyrmecin
Lee, Eun,Yoon, Cheol Hwan
, p. 479 - 482 (2007/10/02)
(+)-Dihydronepetalactone and (+)-iridomyrmecin were synthesized from the stereoselective Favorskii rearrangement product of (+)-carvone chlorohydrin.
